Transcript:

Speaker: Ross Simmons first hit on the art of the side hustle back when his main hustle was being a high school student.

Ross: My first side hustle would have been selling du rags out of my locker when I should have been focusing on my marks. Went to a store, found a bunch of du rags for sale that were a variety of different colors and they had a whole bunch of styles that you just couldn't get out of a traditional store. I took my entire allowance, bought a bunch of them, and then just started selling the du rags out of my locker which was awesome. I was the cool kid at school, it was unreal, so that was really my eye-opener to this power of like a side hustle.

Speaker: After the durag business he ran an online fantasy football league. When he was in university he had customers all over the world. While business was booming, his business school marks were suffering so his mom, in whose basement he was living at the time, made him shut the whole thing down. Such is the plight of the young side hustler. Still Ross graduated with a marketing degree in 2009 and these days-

Ross: I made digital marketing strides as an entrepreneur. I've run three companies; a consulting business, an e-commerce site, and an app called Crave.

Speaker: Ross is also the author of a book called, The Hustle Manifesto, Escape the Nine to Five in Six Months or Less. He's a guy who knows his stuff. The consulting business is his full-time job these days, but he seems to have endless energy for starting up little businesses on the side. What's his secret?

Ross: I have lots of coffee, hence the reason one of my side hustles now is a coffee company. The coffee definitely keeps me running for a long period of time, late nights and early mornings, but that's why I started a coffee company too.

Speaker: Do I need to point out that we met up at a busy coffee shop which was his choice? He didn't even mention that coffee company hustle and grind in his initial rundown of businesses he owns. My first question for Ross, why run a business on the side anyway? Why not just quit the day job and launch yourself full force into the future?

Ross: When you're working your nine to five, you have to kind of stay within a box. Your manager, the CEO, they tell you exactly what you have to do. When you have a side hustle you have full control, so by having full control over this thing you can experiment and try different things that you wouldn't be able to do in your nine to five.

Speaker: So the benefit there, Ross says, is that you still have that steady paycheck to fall back on while you're learning and making mistakes in your side hustle, and that keeps the pressure off your little business to be able to sustain you right away. Next, Ross says, focus and perspective are a side hustlers best friends.

Ross: Don't start thinking that you can boil the ocean. A lot of people go into creating their side hustle thinking they need to create the next Facebook, create the next Snapchat, the next big agency. Start small. Your first step might be just getting your website set up, your first step might be just getting that one client. You don't need to think about what it looks like to get a hundred client, focus on that one thing that you need to do first. If you're selling soap at a farmers market, focus on making soap.

Speaker: Like, really focus he says, boil down what's absolutely essential to get done at your day job, so you don't get fired, and what's absolutely essential for your side hustle to make it a success. Look at your life, see where you're wasting time, if that long commute to work isn't working for you, maybe it's time to move and speaking of moving, make sure you're always moving forward.

Ross: Find those things that do move the needle, and only do those. If Twitters not doing things for you and you're tweeting all the time, you're probably wasting your time so stop tweeting. Focus on something that's actually going to move the needle for your business and allow your side hustle to eventually become that main hustle.

Speaker: Now some of the things that move the needle for your business might be things you're not actually that good at. Ross says that's okay, just because it's a side hustle doesn't mean you have to do it all yourself. It's better to know your strengths and your weaknesses, and get help with the latter. If you're not great at bookkeeping, for instance, hire a bookkeeper. Now finally, when do you know it's time to actually make the move from employed by someone else to self employed. You can get totally impatient and just jump into it or, better, Ross says you can calculate your burn rate, that's the amount of money you need to earn each month in order to live the way you want to live.

Ross: When you've got to a point where you can last at least three months running off of your side hustle at a minimum, then I think it's time to make the jump, because then you have three months to really make this thing work, and you are going to hustle so hard in those first three months that you will probably blow away your own expectations of what you even thought you were going to be able to do.

Speaker: In the meantime you have to keep in mind there are sacrifices when you're working the side hustle.

Ross: You can't always be going out and having a great time and that hurts because everybody suffers from FOMO once in awhile. The fear of missing out, and when that takes place, it's just like you're at home, you're on your computer, your friends are uploading facebook, they're sending you Snapchats of them having a good time while you're on the grind.

Speaker: That grind can really wear you down, Ross says.

Ross: The world of self employment is a complete roller coaster. You surround yourself with people who have gone on the journey, so you can have an authentic conversation with them, and you'll be able to come out of it all right. It is a wild ride, so keep having wild dreams, and drink lots of coffee.

Speaker: So in addition to those wild dreams remember, Ross cautions you against trying to boil the ocean, just start small. Remember to move the needle, remember to get help from experts, and yes, when in doubt, drink another coffee.

About TGIM: TGIM is a podcast for people who can’t wait for the week to start. In each episode we’ll be bringing you inspirational stories about entrepreneurs who have overcome obstacles, built incredible businesses, and are now living the life they want.